Sodium Carbonate → methyl 4-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-2-furancarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Methyl 4-bromofuran-2-carboxylate	HCID 12239443	—
Reactant	1-ethyl-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 57826915	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	methyl 4-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-2-furancarboxylate	HCID 57826697	80.5%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a solution of methyl 4-bromo-2-furancarboxylate (500 mg, 2.439 mmol) in THF (5 mL) was added aqueous Na2CO3 (2N, 3.6 mL, 7.2 mmol), PdCl2(dppf) (160 mg, 0.22 mmol), and 1-ethyl-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (700 mg, 2.96 mmol). The reaction mixture was heated to 70° C. in a sealed tube. After 2 h, the reaction mixture was concentrated under vacuum and purified on silica (EtOAc/Hex, 20-40%) to afford the title compound (460 mg, 76%) as a light yellow solid: LC-MS (ES) m/z 235 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946278B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-046c0ce16817466f87a17f767696542f
Source note	uspto-grants-2015_02